Summary
Virginia, one of the first states established by European settlers crossing the Atlantic, features a stunning coastline along with majestic mountains rich in the history of America’s founding. This state offers a diverse array of experiences, including boutique wineries, breweries, outdoor sporting activities, and picturesque towns with unique shops and local dining options that are sure to satisfy. Take the opportunity to immerse yourself in the state’s history and enjoy a retreat into Virginia’s rural areas. Don’t forget to appreciate the local culture and travel light, allowing yourself to unwind and disconnect from daily stresses.
Explore our selection of the top small towns to visit in Virginia:
1. Abingdon, Virginia
Situated in Washington County, Abingdon boasts a vibrant artistic community and is recognized as a Virginia Historic Landmark. Here, Black’s Fort was constructed for the protection of settlers during the Revolutionary War against local tribal attacks. Today, it stands as a popular destination nestled in the Appalachian Mountains.
For hiking enthusiasts, the Virginia Creeper Trail, spanning 35 miles, originates in Abingdon and meanders through Whitetop Mountain. Stroll down the historic Main Street to visit sites like Martha Washington Inn. Consider an overnight stay and continue exploring local art galleries or the William King Art Museum. Ensure you catch a performance at the Barter Theatre and participate in the Virginia Highlands Festival, a celebration of Appalachian art. Journey down the Crooked Road to immerse yourself in the music and traditions of the mountain communities before concluding your visit to Abingdon.
2. Bristol, Virginia
Bristol, a town uniquely divided between Virginia and Tennessee, features its state line running down Main Street. Situated along the renowned “Crooked Road,” it is celebrated as the birthplace of country music, with the initial recordings of the genre for national distribution made here. Visitors can explore the Birthplace of Country Music Museum or enjoy live performances.
For those less inclined towards country music, activities such as horseback riding or hiking are available. Additionally, you may wish to visit the Bristol and Appalachian Caverns, where the natural scenery rivals the musical charm. Opposite in Tennessee lies the Bristol International Speedway, a must-see for NASCAR fans.
3. Culpeper, Virginia
Notably, Culpeper, located in Culpeper County, was initially surveyed by a young George Washington. During the Revolutionary War, the town provided refuge for pro-Independence supporters. It serves as an ideal weekend retreat for history enthusiasts, encompassing several quaint Bed and Breakfasts.
Visit Old House Vineyards or Belmont Farms Distillery to sample local specialties. Notably, Belmont is the only distillery in Virginia legally permitted to produce moonshine. Alternatively, stroll along the revitalized Main Street, explore local shops, and visit the Museum of Culpeper History. After appreciating the historic homes and churches, consider attending a horse show at Commonwealth Park.
4. Farmville, Virginia
Do not confuse Farmville with the popular Facebook game; it is a town located along the Appomattox River and High Bridge Trail State Park. Despite its growth, Farmville maintains a laid-back atmosphere, making it an ideal getaway for a short trip.
Dedicate a day to explore High Bridge Trail State Park, which extends approximately 4 miles and concludes at the historic High Bridge. Alternatively, spend time in town visiting the Farmville Historic District or Sayler’s Creek Battlefield. Annually, Farmville hosts the Heart of Virginia Festival, highlighting local customs and featuring a fireworks display. If you are unable to attend this event, consider visiting on the first Friday of the month to partake in concerts and community celebrations at Riverside Park.
5. Damascus, Virginia
Nestled in the mountains of Washington County, Damascus is where four prominent hiking trails converge: The Appalachian Trail, US Bicycle Route 76, The Iron Mountain Trail, and The Virginia Creeper Trail. Be sure to pack your hiking boots and camera when visiting this beautiful location!
Each May, Damascus hosts the Trail Day Festival, the largest gathering for Appalachian hikers in the country. Even for those not actively engaged in hiking, the scenic surroundings are mesmerizing. Consider staying in a local cabin to unwind after a day of hiking, biking, or kayaking on the nearby river. Enjoy a coffee at Mojoe’s Trailside Cafe and Coffeehouse, where you can interact with locals or fellow hikers passing through. The small-town vibe allows you to connect with the community, enjoying a relaxed meal in one of the local eateries.
6. Gordonsville, Virginia
Gordonsville is located in Orange County, Virginia, northeast of Charlottesville. The town celebrated its bicentennial in 2013, marking the appointment of Nathan Gordon, a local innkeeper, as postmaster. It also holds historical significance from the Civil War due to its proximity to the Virginia Central Railroad.
Enhance your historical knowledge by strolling through Gordonsville. Visit Nathan Gordon’s original tavern, which was reconstructed as a hotel before the Civil War and served as an army hospital, treating over 70,000 patients. Today, it operates as the Civil War Exchange Museum, worthy of a visit. During the Civil War, the town largely remained unscathed as the Confederate army managed to defend it. Indulge in some lighthearted enjoyment at local shops and galleries or explore the surrounding countryside by foot, bicycle, or horseback.
7. Lexington, Virginia
Lexington, which derives its name from Lexington, Massachusetts, the site of the first shots fired in the Revolutionary War, has also played a pivotal role in American history. The burial sites of Confederate generals Robert E. Lee and Stonewall Jackson are located here, and Jackson’s residence has been converted into a museum. Additionally, Cyrus McCormick invented the mechanical reaper in this town, and his farm is now part of Virginia Tech.
Experience Lexington’s historic Civil War sites and military museums. The downtown area is a historic district filled with charming shops and eateries favored by both locals and visitors. This location has also appeared in the filming of Hollywood productions, including Brother Rat, featuring Ronald Reagan, and Sommersby with Richard Gere. Whether your interests lie in history or cinema, this town presents ample offerings for exploration.
8. Manassas, Virginia
For those familiar with U.S. history, the first major battle of the Civil War, referred to as the Battle of Manassas or Bull Run, occurred nearby. This strategic location was significant due to its railroad crossings, and it was primarily occupied by the Union Army, aside from key battles.
Today, visitors arrive in Manassas to retrace historic steps by exploring the battlegrounds while discovering additional attractions. After observing the battlefield, consider visiting the Manassas Museum or Train Station. Enjoy a refreshing beverage while reflecting on your historical discoveries at Heritage Brewing Company. The historic downtown district offers numerous shopping opportunities as well.
9. Occoquan, Virginia
Located in Prince William County, Virginia, Occoquan sits adjacent to Washington D.C. For those seeking tranquility after the vibrancy of the capital, this town offers a serene escape. The name is derived from an Algonquian term meaning “end of the water,” highlighting its location along the Occoquan River, which served as a vital trading hub for Native Americans and subsequent European settlers.
Presently, Occoquan is a quaint artist community featuring a historic downtown replete with shops and dining options. Spend time strolling along the river and nearing the port, or partake in one of their renowned ghost tours if you dare. For relaxation, consider a visit to the Dansk Day Spa if you find the experience overwhelming.
10. Onancock, Virginia
Originally established as a port town, Onancock lies on Virginia’s Eastern Shore. With stunning waterfront vistas, the downtown area features tree-lined streets and beautiful Victorian homes. This vibrant location offers live music during weekends along with a variety of shops that are sure to impress visitors, complemented by upscale accommodations inviting relaxation and rejuvenation.
Consider an extended stay at the Charlotte Hotel, an upscale establishment, and explore the local art exhibits while walking along the Eastern Shore. The area is also in proximity to Chincoteague and its famous wild ponies. Enjoy a coffee at Bizzotto’s Gallery Café before making your way down to the wharf for a refreshing breeze. Take a boat out on the water to savor the sunset before returning to town.
11. Orange, Virginia
Orange serves as the county seat of Orange County, Virginia, founded in the 18th century. It held strategic significance during the Civil War, serving as headquarters for Robert E. Lee from 1862 to 1864. History enthusiasts may wish to visit St. Thomas Episcopal Church, where Lee worshipped during that period.
Explore the historic downtown district and view the county courthouse before enjoying a stay at the Holladay Bed and Breakfast. Following your exploration, discover the James Madison Museum or visit his plantation home nearby, Montpelier. Consider kayaking along the Rapidan River or stopping by local wineries for a glass of wine.
12. Chincoteague, Virginia
Notably featured in Marguerite Henry’s book, Misty of Chincoteague, the town of Chincoteague itself lacks the ponies made famous in the story, as those reside on the adjacent Assateague Island. According to legend, these ponies survived a Spanish shipwreck. Attend the Pony Penning Day event, where feral ponies are rounded up to swim across the shallow channel between the islands.
Spend leisurely hours at the beach while breathing in the ocean air, and explore the town’s unique shops and ice cream parlors. Chincoteague allows visitors to relive the nostalgic magic depicted in the story. Choose between staying at a local bed and breakfast or coming prepared for camping adventures.
13. Washington, Virginia
Named in honor of George Washington, the town of Washington resides in Rappahannock County and was surveyed by Washington in 1749. It is crucial to differentiate it from Washington D.C., located 70 miles away. The town also served as a hospital for wounded soldiers during the Civil War.
After the war, not much has changed in Washington; it retains a historical rural essence. A weekend here allows visitors to disconnect from modern technology. For a luxurious experience, The Inn at Little Washington offers fine dining and accommodations. Relish exquisite meals and explore the charming artist shops throughout the town.
14. Woodstock, Virginia
Located in Shenandoah County, Woodstock may not be noted for the famous love festival of the sixties, yet it has played a significant role in American history. According to legend, at the onset of the Revolutionary War, a local pastor delivered his sermon, then revealed a military uniform beneath his clerical robes, rallying the men to fight for their newfound country.
Today, visitors can explore historic downtown Woodstock, which features the oldest courthouse still in operation west of the Blue Ridge Mountains—a limestone building originally commissioned by Thomas Jefferson. Make a stop to learn about the town’s rich background or visit the Woodstock Shenandoah Museum or enjoy a beverage at the Woodstock Brewhouse.
15. Wytheville, Virginia
Situated in the scenic southern Blue Ridge Mountains, Wytheville is named after George Wythe, a signer of the Declaration of Independence. This charming town showcases a captivating Historic District and an inviting small-town atmosphere, encouraging visitors to linger longer.
Explore local markets to sample freshly sourced produce or bring your motorcycle to navigate the many scenic trails surrounding the town. If you opt to stay on foot, enjoy an evening of entertainment at the Wohlfahrt Haus Dinner Theatre or listen to live music at local venues. Wytheville offers excellent fly fishing opportunities and numerous nature trails for outdoor enthusiasts. Known for its distinctive name, Wytheville ensures an enjoyable visit for all.
